Tertiary alkanolamines containing surface active alkyl groups

Abstract

The present invention relates to novel tertiary alkanolamines useful as catalysts for preparing polyurethane foams and as additives to reduce the dynamic surface tension of aqueous solutions. The tertiary alkanolamines may be represented by formula (I): wherein A, R<SUP>1</SUP>-R<SUP>6</SUP>, and n are defined herein, and where the tertiary alkanolamine is acid-blocked with a carboxylic acid.

The invention claimed is: 
     
       1. A compound represented by formula (I):                  
 wherein A represents CH or N; 
 R 1  represents hydrogen and R 6  represents —CH 2 C(R 7 )(OH)CH 2 OR 8 ; or 
 R 1  represents                  
 
 
       and R 6  represents —CH 2 C(R 7 )(OH)CH 2 OR 8 ; or
 R 1  represents —CH 2 C(R 7 )(OH)CH 2 OR 8  and R 6  represents an alkyl or alkenyl group having C 4 –C 36  carbon atoms; or 
 R 1  represents hydrogen and R 6  represents —CH 2 C(R 7 )(OH)R 8 ; or 
 R 1  represents                  
 
 
       and R 6  represents —CH 2 C(R 7 )(OH)R 8 ; or
 R 1  represents —CH 2 C(R 7 )(OH)R 8  and R 6  represents an alkyl or alkenyl group having C 4 –C 36  carbon atoms; 
 R 2  and R 3  each represent hydrogen or an alkyl or alkenyl group having C 1 –C 6  carbon atoms; 
 R 4  and R 5  each represent an alkyl group having C 1 –C 6  carbon atoms when A represents N; or 
 R 4  and R 5  together represent a C 2 –C 5  alkylene group when A represents N; or 
 R 4  and R 5  together represent a C 2 –C 5  alkylene group containing NR 10  or NR 11  when A is CH or N, where R 10  is hydrogen or an alkyl group having C 1 –C 4  carbon atoms and R 11  is an alkyl group having C 1 –C 4  carbon atoms or                  
 
 R 7  represents hydrogen or an alkyl or alkenyl group having C 1 –C 5  carbon atoms; 
 R 8  represents an alkyl or alkenyl group having C 4 –C 36  carbon atoms or —COR 9 , where R 9  represents an alkyl or alkenyl group having C 3 –C 35  carbon atoms; and 
 n is an integer from 1 to 3, and where the compound is acid-blocked. 
 
     
     
       2. The compound of  claim 1 , wherein R 1  is hydrogen or                  
 
     
     
       3. The compound of  claim 1 , wherein R 2  and R 3  are hydrogen. 
     
     
       4. The compound of  claim 1 , wherein R 4  and R 5  are alkyl groups having C 1 –C 6  carbon atoms when A represents N. 
     
     
       5. The compound of  claim 1 , wherein R 4  and R 5  together represent —CH 2 CH 2 N(CH 3 )CH 2 —. 
     
     
       6. The compound of  claim 1 , wherein R 7  is hydrogen. 
     
     
       7. The compound of  claim 1 , wherein R 8  is an alkyl or alkenyl group having C 4 –C 22  carbon atoms or —COR 9 . 
     
     
       8. The compound of  claim 1 , wherein R 9  is an alkyl or alkenyl group having C 3 –C 22  carbon atoms. 
     
     
       9. The compound of  claim 1 , wherein n is 2 or 3. 
     
     
       10. The compound of  claim 1 , wherein the compound is selected from the group consisting of N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octadecyl ether) amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octadecyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexadecyl ether) amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexadecyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecyl ether) amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecyl ether) amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-decyl ether) amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-decyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octyl ether) amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-2-ethylhexyl ether) amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-2-ethylhexyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexyl ether) amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hexanol) amine, N-(3-dimethylaminopropyl)-N-(2-hexanol) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-octanol) amine, N-(3-dimethylaminopropyl)-N-(2-octanol) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-decanol) amine, N-(3-dimethylaminopropyl)-N-(2-decanol) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-dodecanol) amine, N-(3-dimethylaminopropyl)-N-(2-dodecanol) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-tetradecanol) amine, N-(3-dimethylaminopropyl)-N-(2-tetradecanol) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hexadecanol) amine, N-(3-dimethylaminopropyl)-N-(2-hexadecanol) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-octadecanol) amine, N-(3-dimethylaminopropyl)-N-(2-octadecanol) amine; N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl butyl ether) amine; and N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-neodecanoic ester) amine. 
     
     
       11. The compound of  claim 10 , wherein the compound is selected from the groupconsisting of N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octadecyl ether) amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octadecyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexadecyl ether) amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexadecyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecyl ether) amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecyl ether) amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-decyl ether) amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-decyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octyl ether) amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-2-ethylhexyl ether) amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-2-ethylhexyl ether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexyl ether) amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexyl ether) amine; N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl butyl ether) amine; and N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-neodecanoic ester) amine. 
     
     
       12. The compound of  claim 11 , wherein the compound is N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl butyl ether) amine. 
     
     
       13. The compound of  claim 11 , wherein the compound is N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-2-ethylhexyl ether) amine. 
     
     
       14. The compound of  claim 11 , wherein the compound is N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecyl ether) amine. 
     
     
       15. The compound of  claim 11 , wherein the compound is N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecyl ether) amine. 
     
     
       16. The compound of  claim 11 , wherein the compound is N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-neodecanoic ester) amine. 
     
     
       17. The compound of  claim 11 , wherein the compound is a mixture of N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecyl ether) amine and N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecyl ether) amine. 
     
     
       18. The compound of  claim 1  in which the composition is acid-blocked with a carboxylic acid. 
     
     
       19. The compound of  claim 18  in which the carboxylic acid is formic acid, acetic acid, 2-ethyl-hexanoic acid, gluconic acid, or N-(2-hydroxyethyl)-iminodiacetic acid.